Boots for steep hills? Are logger boots worth it?

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It’s weird how comfortable the thin rubber boots are. Definitely would need to be careful as theres literally no protection. Everything was based on how quickly a guy could escape death or injury. LNI never bothered us on the matter up in the high country unless there was an event. Most guys didn’t wear chaps or ear protection.It’s a very different world in big old growth on extremely steep ground. Seen some crazy stuff. Everything changed when we switched into second growth. Loved chaps for saving my pants from wear and started using ear plugs. Love them. Never could wear eye protection. Almost killed myself trying
The leather isn't exactly offering any protection over the rubber, unless it is protected. Class 3 boots are the highest rated in terms of cut/chainsaw resistance, and there are offerings available in rubber. My next pair of work boots will probably be (broken link removed to https://www.ebay.com/itm/143400174290) There are more options in Europe for some reason.
 
Ya, a lot of rigging guys wear the Vikings. They definitely add more protection not just for chainsaws but sharp limbs and such. The rigging is brutal on shoe wear. Heavy though. Don’t really hold up as good as you’d think by the looks of them. About 1 season even cutting timber.
 
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Don’t your feet sweat a lot more, or at least stay wetter when they do, in rubber boots?

I guess a hundred generations of your ancestors couldn't have been all-wrong, in choosing leather, goose down, and wool. Each time I go back to one of these traditional choices, I'm surprised they still compete against our modern hi-tech materials.
 
I worked with some freakishly tough old guys that could wear them all year. One guy made it on to a Rainier beer commercial before the owl shut everything down and cutting trees was heavily frowned upon. Saved his life once when we were working in a set. He never wore gloves and his hands look like grizzly paws
 
For everyday boots I like Asolo
 
Don’t your feet sweat a lot more, or at least stay wetter when they do, in rubber boots?

I guess a hundred generations of your ancestors couldn't have been all-wrong, in choosing leather, goose down, and wool. Each time I go back to one of these traditional choices, I'm surprised they still compete against our modern hi-tech materials.
My feet sweat a lot LESS in rubber boots than leather. Our ancestors didn't have modern rubber boots, but most of their material choices actually perform better than our fancy petrochemical synthetic textiles. I've walked and run countless miles in tall lace up leather boots, worn many pair down into nothing. It's not like I'm switching from cheap leather boots to cheap rubber boots either. Even in summer I prefer an uninsulated pair of steel toe Xtratuffs for farm chores and cutting.
 
When I was younger I liked the Chippewa Bollville (?) insulated, 9" logger boot. Wore the soles down to point I had them re-soled. But they are heavy, not comfortable, and the high heel causes my back to ache by end of day, especially when standing on hard surfaces.

For everyday boots I like Asolo - (broken link removed)
They're light, comfortable, and a great fit for my foot (European made), and provide good stability on rough terrain.

I have a tough time finding safety boots that are comfortable. Often a model I like is discontinued.
For safety boots I found a pair that are very comfortable - Cervino Wood Boots By Andrew
After collecting numerous safety boots that I can't/ won't wear because they are so uncomfortable this boot came highly recommended.
Leather boot (Perwanger leather plus Superfabric) fits like a glove (Italian made), light, with good grip and stability. They have a higher top than a hiking boot. Probably as comfortable as can be for a steel toe safety shoe, but pricey (I got discount from list price). While comfortable enough to wear throughout the day, they aren't flexible enough that you'd want to throw them on for a light jaunt.
 
The link to Asolo in my post (#33) might be bogus.
 
Hey, I feel your struggle! While I never encountered any issues when I was younger, I started experiencing severe pain while working on steep hills. The pain in the ankle is absolutely killing me! To make it worse, I also had surgery on my left ankle a couple of years ago. From my own experience, I can definitely say the Timberland boots are by far the best option for logging uneven terrain. Cheers!
I also think they're absolutely gorgeous! While they're obviously not as light and stylish as a brand new pair of yeezy (lol), I quite recommend trying them. Cheers!